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All listings in Annapolis

Search yacht rentals in Annapolis, Maryland.

Page 1 of 121 listings

Private Yacht Charter: On 40ft Regal Commodore
Events in Selby-on-the-Bay · 10 guests

Private Yacht Charter: On 40ft Regal Commodore

5.0
$300/hour
50ft Catamaran Charter with Water Toys - Annapolis, MD
Sailing in Annapolis · 12 guests

50ft Catamaran Charter with Water Toys - Annapolis, MD

5.0
$450/hour
Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways
Events in Annapolis · 8 guests

Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways

5.0
$250/hour
Charter 44' Orana Cruising Catamaran In Deale, Maryland
Sailing in Deale · 10 guests

Charter 44' Orana Cruising Catamaran In Deale, Maryland

5.0
$450/hour
Instant Book
43ft Cruiser Express Yacht for Daily Charter
Events in Selby-on-the-Bay · 8 guests

43ft Cruiser Express Yacht for Daily Charter

5.0
$400/hour
Charter 42' Lagoon Catamaran in Annapolis, MD
Sailing in Edgewater · 12 guests

Charter 42' Lagoon Catamaran in Annapolis, MD

5.0
$425/hour
50ft Catamaran Charter with Water Toys in St. Michaels, MD
Sailing in Saint Michaels · 12 guests

50ft Catamaran Charter with Water Toys in St. Michaels, MD

New
$525/hour
Relaxing Excitement of the Chesapeake Bay and tributaries on our Yacht
Events in Annapolis · 6 guests

Relaxing Excitement of the Chesapeake Bay and tributaries on our Yacht

New
$300/hour
Cruise the South River on 46ft Meridian Sedan Bridge Yacht
Events in Annapolis · 6 guests

Cruise the South River on 46ft Meridian Sedan Bridge Yacht

New
$255+/hour
Discover the Spirit of the Chesapeake Bay with our Nautical-Themed Photography
Events in Annapolis · 6 guests

Discover the Spirit of the Chesapeake Bay with our Nautical-Themed Photography

New
$255/hour
Enjoy a Luxurious Boat Cruise on the Chesapeake Bay, Maryland
Events in North Beach · 8 guests

Enjoy a Luxurious Boat Cruise on the Chesapeake Bay, Maryland

5.0
$400/hour
45' Catamaran Tour Boat in Annapolis - BYOB Private Cruise - 32 Guests Capacity
Powerboats in Annapolis · 32 guests

45' Catamaran Tour Boat in Annapolis - BYOB Private Cruise - 32 Guests Capacity

New
$440/hour
Beneteau Oceanis 45 Sailing Yacht in Chesapeake Bay!
Sailing in Annapolis · 10 guests

Beneteau Oceanis 45 Sailing Yacht in Chesapeake Bay!

New
$232+/hour
FOUNTAINE PAJOT HELIA 44 CATAMARAN
Sailing in Annapolis · 12 guests

FOUNTAINE PAJOT HELIA 44 CATAMARAN

New
$400+/hour
SLOWDOWN - DUFOUR 430
Sailing in Annapolis · 12 guests

SLOWDOWN - DUFOUR 430

New
$250+/hour
2014 CATALINA 445 Sailboat for Amazing Day in Chesapeake Bay!
Sailing in Annapolis · 12 guests

2014 CATALINA 445 Sailboat for Amazing Day in Chesapeake Bay!

New
$250+/hour
Sail the Sea on the Pintita
Sailing in Annapolis · 20 guests

Sail the Sea on the Pintita

New
$500+/hour
Pershing 65 Power Mega Yacht Rental in Stevensville, Maryland
Events in Stevensville · 6 guests

Pershing 65 Power Mega Yacht Rental in Stevensville, Maryland

New
$550/hour
Romantic Sunset Champagne Cruise on the Chesapeake Bay - 2 Hours
Sailing in Saint Michaels · 6 guests

Romantic Sunset Champagne Cruise on the Chesapeake Bay - 2 Hours

New
$400/hour
New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland
Sailing in Annapolis · 13 guests

New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland

New
$1,100/hour
Maxum 30ft Yacht! Escape for a day on the Chesapeake
Events in Selby-on-the-Bay · 6 guests

Maxum 30ft Yacht! Escape for a day on the Chesapeake

New
Snoozed - Active 02 May 2025

Motor Yacht Reviews in Annapolis

  1. EB

    Ernest

    Private Yacht Charter: On 40ft Regal Commodore

    GREAT experience!!! Captain Dennis was terrific. He was professional, yet fun & extremely well prepared. The yacht was clean & well maintained with all the amenities that we could ask for. Our only regret is that we did not book a longer cruise on Seas the Day.

  2. Abigail

    Abigail

    Private Yacht Charter: On 40ft Regal Commodore

    Captain Dennis was exceptional—punctual, professional, and allowed us to have a great time. The boat itself was in perfect condition, with all the necessary equipment and some luxurious extras, like the floating 🏝️, that made the day truly enjoyable. The excellent service and the beautiful setting made it an unforgettable birthday party. I highly recommend Captain Dennis for anyone looking to host a memorable and top-notch maritime event.

  3. Jordan

    Jordan

    50ft Catamaran Charter with Water Toys - Annapolis, MD

    Captain Deren and the crew were amazing — they made my birthday so special. They were super accommodating the entire day for everyone! They were even kind enough to put up some birthday decorations for our group. I’m definitely going to be booking with Captain Deren again!

  4. MT

    Marija

    Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways

    We had a wonderful time at Captain McCoy’s boat. The boat is gorgeous, impeccably clean, and very spacious. The Captain played great music (we didn’t bring our own playlist). He found a great spot for our group to take a swim. It was a perfect balance of cruising and swimming and a perfect 2 hr cruise

  5. TS

    Tiffany

    Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways

    Took my husband on a surprise boat ride for his birthday and he loved it!! McCoy was great at communication when I had questions. He took us on a 2 hour boat ride and made the trip so enjoyable and relaxing!! He played music for us and took us to see some beautiful sights. I will definitely be booking all my boat rides with McCoy in the future!

  6. SR

    Sara

    Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways

    We had a great experience with Captain McCoy and his boat. He definitely went the extra mile and was easy to communicate with to set up our trip. We went out of City Dock and toured the coastline, saw Chesapeake Bay bridge and then tied up for some swimming. He had a great float for the kids, and he had some comfy seats for the front of the boat. The shaded table in the back was awesome. Would highly recommend!